


Until We Meet Again

by CaptainParisStarr



Category: Pocket Monsters | Pokemon (Anime)
Genre: Anal Sex, First Time, M/M, Semi-Public Sex
Language: English
Status: Completed
Published: 2015-09-01
Updated: 2015-09-01
Packaged: 2018-04-18 14:00:53
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, Underage
Chapters: 1
Words: 2,875
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4708565
Author URL: https://archiveofourown.org/users/CaptainParisStarr/pseuds/CaptainParisStarr
Summary: <blockquote class="userstuff">
              <p>Ash can't sleep the night before leaving Pallet Town to head to Hoenn. Heading outside, he runs into the last person he expected to find lurking behind his house; Gary Oak! First time PalletShipping Story.</p>
            </blockquote>





	Until We Meet Again

Ash rolled over one last time before throwing the covers off and climbing out of bed. It was no use, he couldn't sleep.

 

No matter how much he tried to convince himself that he needed sleep for his trip to Hoenn the next day, it did him no good. All he could think about was the fact that he was back home in Pallet Town, but Gary wasn't.

 

Gary had left for another region, travelling with only his Blastoise in the hope of becoming a Pokemon Researcher...

 

Since when had Gary ever shown any interest in following in his Grandfather's footsteps? And why had he left without saying goodbye?

 

It was then that Ash realized he had left the house, slipping quietly through the back door to avoid waking his mother up. Glancing around, he began wandering around as aimlessly as the thoughts of Gary swirled through his head.

 

He was also confused as to why Gary leaving without saying a word to him hurt so much. He didn't know when he would ever see Misty again either, yet he was barely thinking about her.

 

“Ash...” The name was whispered, faint. His ears strained for anything more, but all was quiet. Had he only imagined hearing his name?

 

No, wait, a figure was standing over there, by the small copse of trees. Turning towards the figure, he was halfway there and only just able to make out the fact that the figure was male when he turned and fled into the trees. Speeding up, Ash caught up with the figure in the heart of the copse, well out of sight from his house.

 

“Ash, no you shouldn't be out here...” As the words reached his ears, Ash gasped as he recognized the boy.

 

“Gary? I was told that you had left already...?”

 

“I had, but...” Gary bit his lower lip, a nervous gesture that Ash had never seen before. “But I turned back once it got dark. I had to see you again, but...” Shaking his head, Gary stopped talking.

 

“But what? What are you scared of?”

 

“Who says I'm scared?” Gary retorted, with a quick smile that let Ash know he had gotten it right. “I'm scared of how I feel... About you...” The last two words were spoken so softly that Ash almost missed them.

 

“About me? Don't worry about me, I'll be fine in Hoenn even if you aren't there to keep an eye on me.”

 

“I know that! Ash, you're smarter than you think you are, and you trust your instincts, so no, I am not worried about you exploring Hoenn, even though I'm heading to Sinnoh. That's not what's scaring me.”

 

“Oh?” Ash frowned, confused. “I'm at a loss, then. If that's not what's scaring you, then what is?”

 

Gary was only barely able to keep his jaw from dropping, he was so surprised. Was Ash really that clueless, oblivious to the fact that Gary had been flirting with him throughout the Silver Conference? He knew that Ash was younger than he was, but only by two months, and Gary had been growing sexually aware of others since he had turned twelve. Now they were both fourteen, and he had never known Ash to be a slow learner, though he was rather scatterbrained and at times obtuse.

 

“I... Ash, please don't make me say it. How can you not know how I feel about you? I thought you came out here because you saw me...”

 

“I came outside because I was restless and unable to sleep. But I didn't see you until I was already outside...” Ash shook his head, still not getting where Gary was trying to go with all this.

 

“Shit...” Gary gritted his teeth and turned away, his fist clenched as though he was fighting with himself.

 

“Gary, please relax and talk to me.” Reaching out, Ash placed his hand on Gary's shoulder, the first physical contact they'd had with each other since leaving Johto.

 

Even that gentle touch undid all of Gary's efforts, and he pushed Ash against the nearest tree, pinning his friend there with his body, as his lips met Ash's. Then he jerked away again, as his mind caught up with his body, his cheeks flaming.

 

“What was that?” Ash whispered, unconsciously touching his tingling lips, his eyes wide with surprise.

 

“It... It's nothing, just forget about it.”

 

“You call a kiss 'nothing'?” Ash asked, cocking his head to one side as he studied Gary intently. Did Gary like him? Was that what this was about? But boys were supposed to like girls right? Then why? And why did Ash want to feel Gary's lips against his own again?

 

“Ash?” Gary had twisted away, but now he was looking straight into Ash's eyes, hope shining in his own. “You didn't hate being kissed by another guy?”

 

“No. It confused me, but that's all.” But Ash blushed as he spoke, wondering if that was really true, as the kiss had made his heart skip a beat.

 

“Are you sure all you're feeling is confusion?” Gary asked, stepping closer once more.

 

“I- I don't know.” Ash confessed softly.

 

Smiling gently, Gary leaned closer once more and this time Ash met him halfway, acting on pure instinct as he had no idea what he was doing. But his confusion only increased as the gentle pressure sent waves of pleasure coursing through his veins. Pulling away, he struggled to breath normally, and twisted his head to the side, his eyes screwed shut, allowing Gary access to nibble his neck.

 

“Gary! S-stop...” Ash eventually panted out.

 

“What's wrong?” Gary frowned as he pulled back, scared that he had crossed the line and done something that Ash didn't like or wasn't ready for.

 

“Should this feel so good? I mean, we are both male and... and this is confusing...” Ash whispered, hugging himself and staring intently at Gary's feet.

 

“Ash...” Laughing softly, Gary reached over and grabbed his friends chin, lifting it up until Ash was forced to meet his eyes. “That doesn't matter. Sex doesn't have to be between a man and a woman; as long as two people like one another in that way their genders don't matter.” Gary explained gently. “And I like you; I want to pleasure you Ash, but only if you also want me to. If you don't then we can stop this here and now, but if you do...” He broke off, uncertain what he was asking for.

 

“Oh...” Ash felt his face heat as he realized what Gary was saying, and he felt bad for freaking out.

 

“Do you want to stop?” Gary asked again after waiting for almost a minute for Ash to answer his question. Slowly, Ash shook his head.

 

“No, I don't want to stop. If this is really okay and... and normal, then no. It feels too good to stop.”

 

Releasing a breath that Gary hadn't been aware he was holding, he relaxed. “Good, that's good. If you do want to stop though, just let me know and I will.” Ash nodded even as he leaned in again and kissed Gary again. Then he pulled away.

 

“What happens between two men, uh... in bed?” Ash asked awkwardly, realizing that he had no idea where this would go next.

 

“It would be easier to show you than to tell you verbally. Do you trust me?” Gary hoped that he didn't sound as nervous as he felt, and he prayed that he knew what he was doing as this would be his first time as well.

 

“Have you done this before?” Ash asked suddenly, almost causing Gary to jump as Ash's question eerily echoed his thoughts.

 

“N-no, I haven't. But I have uh... I've watched a couple videos that show guys doing sex stuff together and uh...” Gary blushed hard, surprising Ash who had never seen him so flustered before.

 

“Oh.” Ash laughed. “Well, neither have I. So lets figure this out together, okay?”

 

“Okay.” Gary nodded, happy that Ash wasn't expecting him to be as good in bed as he was at battling. Not yet anyway. “Can I touch you?”

 

“But you're already touching me.” Ash pointed out, frowning as he wiggled his hips to remind Gary that his hands were resting on them.

 

“That's not what I... I mean can I touch your... uh... your cock...” Gary was blushing so hard that he had to choke the words out.

 

“Oh...” Ash had no idea why Gary would want to touch that part of him, but he wasn't against the idea so he nodded. “Okay yeah you can touch that if you really want to.” Ash replied slowly, his confusion showing.

 

“Ash? Uh... do you play with yourself at all?” When Ash only looked at him blankly Gary sighed. “Do you play with your cock?” He asked, still embarrassed but not wanting to beat around the bush any longer.

 

“No. Should I?” Ash frowned harder as he wondered why Gary was asking such an odd question.

 

“Ash... it feels really good.” Gary whispered, shyly moving his hand until it was resting on Ash's stomach just above the waistband of his boxers.

 

“Does it? How does it feel good? Can you uh... show me?” Ash asked, giving Gary all the permission he needed to reach inside Ash's pants and gently grab his cock. Ash gasped at the contact, then had to bite his lip as Gary stroked him gently, causing the organ to swell with blood.

 

“Ash, relax, this is normal. Let yourself get hard.” Gary whispered as he realized that Ash was not tensing in pleasure.

 

“What's happening to me?” Ash panted as he felt the pleasure of Gary's hand mingle with confusion at his bodies reaction.

 

“You're getting an erection; don't worry its normal. It means you're sexually aroused that's all. Just relax and let me pleasure you...” Gary loved that he was the first one pleasuring Ash though, and he had to hide a smile as he reached down with his free hand to push down Ash's boxers.

 

“Gary!” Ash shrieked as cold air hit his now-exposed member.

 

“You're beautiful, Ashy-boy, there is no need for you to be shy or embarrassed. Here...” Gary pulled away reluctantly and dropped his pants, revealing his own erection. “You can see me as well.” Guiding Ash's hand to him he moaned softly as Ash gently touched him. He was surprised though at how much better it felt to have Ash's hand on him rather than his own. Then he resumes stroking Ash gently as he leaned in to steal another kiss.

 

“What comes next?” Ash asked, panting as Gary showed no signs of pushing things further.

 

“Do you really want to know? Ash... I don't want to do anything you're not ready for...”

 

“Yes, I want to know. You can do whatever you want to me as long as it doesn't hurt.” Ash flashed what he hoped was a reassuring smile as Gary pulled away.

 

“Turn around then.” Confused once more, Ash did as Gary had asked. “Now just relax. This might feel odd at first but...” Breaking off Gary shook his head as he pulled Ash's boxers off completely. “Spread your legs.”

 

“Like this?” Ash complied, leaving his underwear on the ground at his feet.

 

“Yeah.” Nervous now, Gary had to take a deep breath to steady his hands before sucking on his pointer finger and rubbing the slick digit over the outside of Ash's rear opening. “How does this feel?”

 

“Weird. Are you sure you know what you're do-ING!” Ash yelped as Gary suddenly pushed the finger inside him, then froze as he glanced back towards Ash's house. The last thing he wanted was for Delia to investigate the noise and catch them like this.

 

“Ash, yes I know what I'm doing; and you have to keep it down. Unless of course you want your mom to see you getting analed by me?”

 

Tensing, Ash glanced back at Gary wide eyed. “What do you mean by 'get analed'?”

 

“I mean... Oh fuck it! Sex between two men involves one of them taking the others cock into his ass. That's why I'm fingering you to uh... to see if you like it and want my cock inside you...” Gary spoke fast, blurting it all out before he had a chance to chicken out.

 

“Gary... What are you saying?” Ash spoke softly and Gary knew that he was not asking about the anal sex.

 

“I... Ash, I think I love you...” Gary confessed, staring at the ground. “That's what was scaring me so much earlier, and why I had to come back and see you. Because I might be falling in love with my best friend and... and I don't know if you feel the same way or ever will...” Gary barely had time to take a shuddering breath before Ash's arms were wrapped tightly around his shoulders.

 

“Gary... Wow I had no idea I meant so much to you. I don't really know what I feel for you, but you are definitely my best friend and...” Ash glanced away, then steeled himself and gazed straight into Gary's green eyes. “I loved what you've taught me about sex so far and I... I want to learn more from you. So yes, you can... put your cock up my ass if you really want to.”

 

“Ash...” This time when they kissed it was different as it was slow and tender as Gary finally gave into the urge to show Ash how much he really meant to him. “I never thought that you would be the one I give up my virginity to. Nor that I'd be the one to take yours. But this feels right, like this is how it should be.” Smiling, Gary gently turned Ash back around before reaching for his bag and pulling out a bottle of lube.

 

“What's that?”

 

“Lube; girls get wet but guys don't and so the wetness must be added. And I use it when playing with myself because it feels better that way.” Kissing Ash's ear he resumed fingering his friend-turned-lover until he could take three fingers without pain, then he lubed up his eager cock. “Ready?”

 

“Yes.” Smiling, Gary thrust into Ash's tight opening, for once not thinking about any possible consequences or regrets, but rather was living in the moment. All that mattered was that Ash didn't hate him for being gay and liking him romantically and while Ash didn't love him back yet he had at least said yes to giving things a try with Gary. The thought made him smile wider as he began gently thrusting his hips as Ash adjusted to the intrusion.

 

Nothing more was said as they made love, Ash biting his lip to keep quiet as Gary unexpectedly found his prostate and Gary pressing his face into Ash's neck to muffle his own cries. Neither had anticipated the level of pleasure sex would generate, and neither wanted the pleasure to end.

 

But end it did, as Gary pounded Ash's prostate one time too many while playing with Ash's cock, causing him to orgasm for the very first time. As Ash came, his muscles tightened around gary and he found himself unable to hold back, flooding Ash with his seed. Then he pulled back and sat down on the ground, tugging Ash into his lap.

 

“I wish I could stay with you, Ash. But others might not understand this; Ash, be careful for many people do view what we just did as wrong or even evil just because we both happen to be male. Besides, we have separate dreams to pursue now and I don't want you to give up on your dream of becoming a Pokemon Master just because I will no longer be your rival. Ash, I know you can do it as long as you have the time and space to do this your way. I have faith in you and... and when you're done exploring Hoenn, come over to Sinnoh. I'll be waiting for you there. Whatever happens, I'll be waiting for the day when I can hold you like this again.”

 

“Gary, I'll do my best for both of us. You can count on it.” Snuggling against Gary, Ash stifled a yawn as he was reluctant to go back to bed, because he knew that if he did Gary would leave and he didn't want that to happen. Now that he knew that Gary treasured him he wanted to stay with him for as long as he could. In the end, Ash fell asleep in Gary's lap and Gary had to clean him up carefully and carry him back to bed, before slipping silently away, knowing that if he was still here when the sun rose that he would never be able to leave, because Ash wouldn't let him.

 

As he walked away though, he was thinking not of the future he had ahead of him, but of the boy he was leaving behind and the promise he had made. Only the thought of being reunited with the boy he loved in Sinnoh kept him walking as he set out to begin his new life as a Pokemon Researcher.

 

End.


End file.
